


Lupin's SPN AU BINGO Card!

by lupinjoallen



Category: Supernatural
Genre: Abuse, Eventual Smut, F/M, Fluff and Smut, M/M, SPN AU Bingo, Self-Harm, Shameless Smut, writing challenge
Language: English
Status: In-Progress
Published: 2018-01-10
Updated: 2018-03-21
Packaged: 2019-03-02 22:35:37
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 13
Words: 14,390
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13327809
Author URL: https://archiveofourown.org/users/lupinjoallen/pseuds/lupinjoallen
Summary: This is a series of stories written from prompts from my bingo card for the SPN AU Bingo Card. Each chapter will have appropriate triggers and will display the square filled!





	1. Square Filled: Free Space

**Summary for the Chapter:**

> When a mark appears on your skin, it’s because your SoulMate has the same mark. Dean feels guilty for all the scars his must see, from hunting and various other stupid stunts. But what kills him is when he wakes up with a what looks like self-harm. But he discovers something else; he can talk to his SoulMate by drawing on his skin!
> 
> Triggers for self-harm and hinted abuse.

Soulmates weren’t rare, but finding them was always difficult. Especially as a hunter. He stared in the mirror one morning, looking over the scars over his body. He had bruised ribs, but he wasn’t sure where they’d come from. But something else was different? What was it?

No cut lip, though, that was the case some months back.

His worry was started to push through until he ran his hand through his hair. He finally saw it. It was hard to make out, but he could see tiny red marks in the shape of a metal lighter head.

Multiple ones over his right arm. He gulped and sighed.

Self-harm, he knew. The cuts on his own thighs he’d made several years ago were evidence of that.

Dean thought to himself, trying to understand what he could do. He wanted to follow the bond, but he wasn’t sure where it’d take him. He didn’t know how to communicate. He thought for a long moment before coming up with a theory.

If he could see the wounds from his soulmate and any marks they’d gotten, and they could see his, would he be able to pass messages?

It was all in theory, but there was no harm in trying. He was trying to think of where to write, sitting in his boxers now on his bed with a black marker in hand. Finally, he chose his thighs. They were easily covered and his mate would be the only one that could see it...hopefully.

Dean got to writing on his right thigh.

“Are you safe?”

It was simple. He wondered if just that little bit would help. He waited and waited. Nothing for the first few minutes. He sighed, laying his hand on his palm when on his left thigh, blue ink began to appear.

Blue...somehow the color soothed him but also worried him as the ink stopped.

“No.”

Dean shuddered and gulped and got to writing under it. His soulmate’s handwriting was so precise and so pretty, but also small and slow. He wondered what was happening on their end.

“Do you want me to take you away?” He’d written.

“It might end badly.” They wrote back.

“But you’d be safe. I live in the safest place on Earth.”

“An underground bunker?” They wrote back.

Dean chuckled as he wrote, “Something like that.”

There was a small blue dot that appeared, bleeding into his skin. They were hesitating. Dean watched the dot and sighed before writing, “Dean.”

“Y/N.”

Another long pause and a blue dot egging him on. It was almost like seeing the typing notification on a cellphone. He blinked and wrote down his number.

After a long while, he’d gotten a text. “Dean?”

“Yeah. Y/N?” He typed back.

He sighed in relief when they replied with a “Yes.” He hesitated, not sure what he could do before sending, “I’m serious about getting you away.”

There was another hesitation before they sent their address. Dean blinked. Illinois. He looked up the address and gulped before sending, “Ten hour drive. Can you hold out? I just gotta get my brother. You might like him. He’s weird though.”  
Y/N sent a laughing emoji to him, making him smile warmly before sending, “Can’t be any weirder than mine.” Then another message, “I’m scared about leaving him here.”

“Is he being hurt?”

“No. I take most of the blows.”

“He can come too. I promise you’ll both be safe.”

He saw the “Sent” at the bottom of his message change to “Read,” but Y/N wasn’t typing anything. He was getting worried before he received, “I’m talking to him. Are you okay with meeting up somewhere close to the house when you do get here? I don’t want any hints about us leaving.”

“Absolutely,” Dean sent before getting up and hurrying to Sam’s room. He banged on the door, shouting, “Sammy, get up. We got a ten hour drive.”

“What?” he heard muffled within the room before the door opened. “Dean, why are you in your boxers?” He squinted, seeing the marker on his skin. “Wait, what--”

“I found them,” He said simply. “Y/N and their brother is in serious trouble. They’re only ten hours away.”  
Sam was awake and nodded, hurrying to dress. Dean smiled and hurried to his room. He checked the messages. Y/N had sent, 

“He’s in. We’ll pack now and hide our stuff in my car.”

“Pack only what you absolutely need. You’re about to disappear off the map for a while. Are you ready for that?” Dean sent. He was admittedly anxious and gulped thickly in thought. What if Y/N changed their mind? What if it’s a trap?

“I’ve been ready for years,” Y/N had sent and Dean was out the door, about to haul ass to the person he was meant for.


	2. Square Filled: Journalist!Sam

**Summary for the Chapter:**

> Sam has been working as a research journalist for years. After an interview with the Ghostfacers, a famed paranormal investigation team, Sam wants to prove those jerks wrong about ghosts. So he partners up with his editor, Y/N, and things get interesting.
> 
> Triggers for smut in this one.

Sam was desperately fighting the urge to roll his eyes as he listened to the two morons babbling and arguing back and forth about a supposed ghost encounter they’d had.

The Ghostfacers. They were blowing up on YouTube. These guys thought it was because they had “quality content” whilst, after three minutes of research, Sam could tell these guys were a laughing stock to the paranormal community. The only thing that kept some viewers tuned in was the drama and the hot girl who seemed a little bit empty headed.

Sam wasn’t quite sure how it happened, but he was the one stuck interviewing him for the magazine, Night Bumps. Admittedly, he loved working for the magazine! It was a magazine that got more ground every Halloween, focusing on horror movies, stories, and even doing coverage on old murder cases that still remain unsolved, like the Black Dahlia! Sam actually had pride in that article as old murder cases were his specialty.

But these guys? These morons claimed to be going after Jack the Ripper’s ghost, despite that his hunting ground was in England.

He was all the more grateful once he was done interviewing them and hurried back to the office, wanting to get this article written and out of his life, once and for all.

“Whoa, where’s the fire, Winchester?” Gabriel, the writer for a lot of religious based articles, asked as Sam hurried by.

Sam sighed. “I just wanna get this article over with.”

“They that bad?” Gabe asked, making a face. Upon Sam’s nod, Gabe hummed in thought before saying, “I’ll meet you at your computer. I think I know someone that can help.”

Sam frowned as the shorter guy hurried off before shrugging. He went to his computer, leaning back in his chair as he opened a new document. How did he even start this piece of crap article? It wasn’t like he was excited about it. Frankly, the guys (What were their names again?) just irritated him to all hell and he just wanted to write slander against them, but knew it would end badly for him.

“Hey, Sammy,” Gabe cooed, peeking from around the cubicle wall.

Sam sighed. “Dude, quit calling me that.”

“But I got a surprise for you.” He stepped out and out you came. You smiled softly to Sam, looking somewhat sympathetic. Sam gulped a bit and looked to Gabe. He was suddenly really, really glad he never told Gabriel about his raging crush on you. “Y/N’s gonna help you.”

“Oh?” Sam asked softly, raising an eyebrow to you.

You smiled so proudly, Sam swears he would’ve swooned. “Yeah. I actually got assigned an investigation. I’m gonna hit up this old house that supposedly belonged to some old KKK members. Apparently, the leader at the time was killed by an unknown persons of interest.” You waggled your fingers as you grinned, doing the “spooky voice” as you said, “And they say his ghost haunts it to this very day. Ooooooh~”

Gabe snickered as Sam rolled his eyes. “Okay. And what’s this gotta do with me?” He finally asked.

“Give you a taste,” You said, smiling. Sam had to fight the dirty thoughts trekking through his mind as you explained. “I’d like you to tagalong for my little stay in Motel Racist. We’d only be in there for about three hours, midnight to three a.m.”

“Why then?” Sam asked curiously.

“Those are the peak hours of hauntings. At least, in my research,” You admitted, blushing a bit.

God you were adorable when you blushed. You were smiling shyly as you looked to Sam hopefully. Those pretty eyes sucked him in and that’s how he found himself picking you up from your apartment around 11:30 PM.

Now, granted, Sam had always hoped a late night trip to your place would have been after the date he had been wanting to ask you on for ages and he was dropping you off...or staying the night. He wouldn’t be entirely against it.

You bounced out the door and hopped into his car, giving him a can of drink. He read the label and frowned. “An energy drink?” He asked, raising an eyebrow to you then staring in both shock and horror when he saw that you were chugging down yours.

“Yep,” You panted out, licking your lips. “High energy is good. Plus I couldn’t really sleep when I tried napping so this’ll do just as well. Drink up.”

“You do know how bad these are for you don’t you?” He asked, worried now about your health. It was no secret you went on these investigations at least once a week, making him wonder how often you actually spent downing these death drinks.

You just rolled your eyes. “Well, duh. That’s why I got the natural fruit ones.” Sam blinked and turned on the dash light, reading the ingredients as you said, “Those Monster drinks make me crash way too hard. These things are great. Bit pricey, but you don’t get that crash. You just need to burn off the energy.”

Sam hummed, glancing to you before downing the drink himself. You smiled gleefully before he started driving. You gave him directions as you both began to feel the buzz of the energy drink. Sam glanced over at you. He hated that the extra energy and watching your excitement turned him on a little. Instead, he focused on the road and pulled up to the supposedly haunted house.

You pulled out some gear from the small bag you were carrying, giving him what looked like some kind of reader before you pulled out a small camera. “Just stay close to me. When there’s a ghost, or something ghostly, that thing should start going off.”

You turned it on and Sam asked, “Is this one of those EMF Readers?”

“Nailed it, Winchester,” You chuckled before leading him inside. “I’m just gonna record so I can have some future reference for my article. Notes, really.”

Sam smiled fondly to you before nodding. “Alright. Let’s get to it then.”

He followed you inside, listening to the EMF Reader hum and whine softly in his hand. His eyes darted over the darkened room. He took in the furniture covered in protective dust cloths that yellowed over time. He hummed as he looked around curiously.

He followed you through the house, frowning when the reader keened loudly. You glanced at him and grinned, nodding to him. “Follow it.” You said encouragingly.

Sam nodded and led the way through the dark house, following the sound of the high pitched whine to the dining room. He raised it up then glanced to you as it rang loudly. He saw your grim expression in the moonlight and frowned. “Y/N?”

“Shut it off,” You said softly. He did so, looking to you worriedly...until you turned on a flashlight. Looking up, he saw frayed and decaying rope hanging from the stair railing. He gulped softly. “As much as I hate saying this, the fact that it reacted to this piece is fascinating.”

Sam glanced to you then nodded. “Kinda messed up.”

“Me or this?” You joked, making him smile. You both shared a chuckle before gasping as a door suddenly slammed shut. Sam immediately grabbed your arm, keeping you behind him. You both listened quietly as the floor creaked, as though someone were walking on it. You shivered as the cold settled in. “Whoa. Bit nippy, isn’t it?” You whispered.

Sam hushed you gently, looking around. He saw his breath and frowned. “We should leave.”

You nodded and moved with him out the back door. The both of you hurried out to his car and got in. Sam drove quickly away from there. After a long while, you both started laughing.

“We high-tailed it so quickly!” You giggled.

“You’re the one that’s supposed to be a big bad ghost spotter!” He snickered.

“Shut up! You’re supposed to fight them and keep me safe, Sammy,” You sighed, smiling big. Sam glanced to you then back to the road, biting his lip. “What?”

“Shouldn’t call me that,” He said, smiling still.

“What? Sammy?” You watched him shift. “Okay. You either hate that nickname...or it’s turning you on.”

“What? I--”

“So which is it...Sammy?” You teased. You leaned closer to him and smirked as you said, “I still gotta burn off that energy drink.”

Sam nearly choked as you trailed your hand along his inner thigh, licking his lips. “I’m driving, Y/N,” He said, pressing his hips up as you cupped his groin. He groaned softly, glancing at you as he felt your breath on his neck. “Y/N…”

“Tell me to stop and I will. But if you wanna fool around, pull over.”

Sam quickly found a place to park before kissing you as he unbuckled his seat belt. Your lips tasted like the fruit from the energy drink and some flavored chapstick you kept. Your hands pushed up into his hair as he tried to pull you closer, swearing under his breath as he realized the cupholders between you both was making this impossible.

You both quickly climbed into the backseat, only to pounce at each other as he laid you out under him. He moaned as your legs snapped up around his waist. “Fuck,” He grunted, grinding into you. “No idea how badly I’ve wanted you.”

You just grinned widely and pressed up against him. “Well c’mon, Winchester. Show me how bad you want me.”

You then gasped as he pushed up your shirt quickly to kiss your chest. You moaned softly, enjoying the feel of his lips. You knew Gabe was up to something when he’d dragged you to Sam’s cubicle earlier that day. It didn’t help that the prankster of the magazine knew about your crush on him, ensuring you every time you tried to ask Sam for anything!

With Sam’s tongue dragging over your sternum as he stripped off your bra and sucked a nipple into your mouth, you realized he was right. You were considering getting the guy a fruit basket.

“No fair,” You whined, pulling off his shirt. Sam smirked to you and kissed you, both of your moaning as your chests pressed against each other. “Fuck,” You whispered, blushing as you saw his body. You figured he was muscular but this guy was ripped!

Sam chuckled. “I could say the same for you,” He teased before reaching up front. He pulled a condom from his wallet, setting it aside. “You sure, Y/N?”

“Hell yeah.”

“How do you feel about me fucking your pretty cunt from behind then?”

Oh holy shit. This guy was going to destroy you just with his words. You nodded with a whine and he quickly flipped you onto your stomach. Your chest pressed into the cool fabric of the back seat and he was quickly tugging your pants and underwear down. You heard his groan of excitement as he saw you were your bottoms caught around your knees, ass in the air for him. He lubed up his finger with his spit before sliding it into your dripping hole.

You groaned as he worked you open, kissing your back and whispering encouragingly to you as he slid in a second finger. You were nearly shaking by the time you heard him undoing his belt and pushing down his own pants. He grabbed the condom and you saw the label on it out of the corner of your eye and gulped. It was one of those Magnum XLs.

The moment he had it on and notched up to your entrance, he’d asked if you were ready, to which you whimpered out a “Yeah,” and pushed in slowly.

“Oh fu--” You gasped, clutching at the door. He was bigger than you thought and you were whining as he kept moving slowly into you.

“God damn,” He moaned, gripping your hips. He had stopped and you whimpered, realizing he wasn’t fully into you. “Gotta...Fuck. You okay?”

“Yeah. Just…” You moaned softly and your head dropped. “Wasn’t expecting you to be that big!”

“Disappointed?” He chuckled before kissing your neck. You grinned and turned your head, kissing him. Sam hummed and pushed in the rest of the way, making you both moan in pleasure.

Every time you’d ever imagined sex with Sam, you always thought he would be gentle and loving. He was always very much aware of his size and would try to become smaller so he wouldn’t scare anyone. Now he was gripping your hips, growling and grunting as he fucked you into his backseat. His arm slid around you and he pressed his chest against your back, grunting dirty words about how good you felt and how hot you looked crying out under him.

“Fuck, Sammy!” You moaned, nails digging into the cushions as you tried to adjust so you could sit more in his lap. Instead, he pulled your hip up, holding you in place. “Oh my god…”

“You look so good taking my cock, Baby,” He moaned, kissing your neck. “Wanna keep fucking you tonight.”

You smiled as you moaned, nodding. “Please,” You begged. “Want...Oh...More!”

Sam groaned and reached between your legs. His fingers moved into your folds, searching until you jerked and mewled. “Right there?” He asked, smirking as he toyed with your clit. “That’s your clit there?”

“Yes, yes, yes!” You chanted, shaking and clenching up.

“Oh that’s it, Y/N. Cum for me. Wanna fuck you proper in my bed!” He moaned, kissing and biting at your back.

You snapped and orgasmed hard, feeling your face flush as he rode out your pleasure and played with your clit until you felt the condom expanding and his cock twitching inside you. His moans and jerks of his hips were your only indication he’d orgasmed with you, surprising you to say the least.

Your breaths came in hot pants and you vaguely noticed the windows had fogged up in your excitement. Sam caught his breath first and kissed the back of your neck gently, squeezing you to him. Finally he smiled. “Catch our breaths then go to my place?”

“Please?” You giggled breathlessly.


	3. Square Filled: Mechanic!AU

**Summary for the Chapter:**

> Castiel Novak is already having a bad day. Then his car breaks down! The only shining light is the hot mechanic is willing to help Cas out. But Cas is broke!
> 
> Triggers for smut!

“God fucking dammit!” Cas shouted, slamming his fists on the wheel.

Worst day in his book. He let out a shaky breath and rested his forehead on the wheel. He wanted to just break down and cry with how frustrated he was. He checked his phone, ready to call for a tow when--

“Of fucking course!” He snarled. One percent battery life! He let out a shaky breath and rubbed his face. He told himself that maybe he could figure it out and he could limp home.

The day rattled in his head, banging and taunting him. He had dealt with that dick Zachariah just bitching on and on about some deal that apparently he’d cost his boss, despite not having even been a part of the meeting of involvement. In the end, the dick was threatening to fire him. Cas had it and said, “You know what. Fuck it. I quit. Save yourself the trouble.”

And now Cas had no job, which honestly wasn’t as bad as it sounded. It was dealing with his asshole of an ex-employer, followed up by some bastard nearly hitting him on his way out of the parking garage. He was just glad he could get his shit before he left.

But as Cas stared at the smoke coming from his engine, he realized how fucked he was.

It was in the midst of him thunking his forehead against the metal hood that a truck rumbled past and pulled over. Cas glanced over his shoulder, seeing that it was a tow truck! He smiled a little, realizing how lucky he was. Some mechanic happened to see him and he was saved!

Out from the truck came the mechanic and Cas had to quickly look away so the man wouldn’t see the flush in his cheeks. “You okay, Sir?” The guy called out.

Cas cleared his throat and finally faced the guy. Bow legs, green eyes, freckles that probably spread all over his body. Holy shit. Cas might lose his cool with this guy walking up to him. He was like some Greek statue come to life.

“Yes, I am alright. My car broke down though,” He admitted, glancing at the engine.

The mechanic smiled. “Well, you want a lift? I can tow you to my shop and we can figure it out from there.”

Cas quickly said, “Yes, thank you! I really appreciate it.”

“Yeah. No problem, man. Why not grab whatever you need from your car and hang out in the truck. Heating works pretty good. Name’s Dean by the way.”

“Cas.” Cas reached into the car as he watched Dean get the lift ready. He grabbed his house keys from the keyring, leaving the car key for Dean to use as needed. But then… “Oh no,” He whispered to himself.

Where was his wallet? Cas searched the usual places, pockets and the middle console between the front seats, before reaching into the glove compartment, the box of his office supplies and even the door.

“Everything okay?” Dean asked. Cas shot up, smacking his head hard against the roof of the car. As he groaned, he could hear Dean choking on a laugh before he cleared his throat. “You good?”

“Yeah. Sorry. I’m fine,” Cas sighed before going towards the truck. He had to take several deep breaths. He sat in the truck, rubbing his arms to warm up and sighed. “I’m gonna be fine.”

He calmed himself down and was about to send out an SOS text to his brother, Gabe, when the power down screen lit up, chiming the shutting down tone, before shutting off.

“...fuck…”

Cas kept quiet the whole ride to the shop, Singer’s Autos as he’d learned, listening only to the radio playing Led Zeppelin. Dean had actually asked him if he’d prefer to change the station, to which Cas politely declined, admitting to enjoying the song. At that, the guy actually turned it up, making Cas relax a bit with a smile.

The shop was empty when they arrived and Cas was starting to feel sick with anxiety. There wasn’t anything he could do about it as Dean pointed him to the office and he sat down. He rubbed his face, trying to calm down.

He didn’t notice Dean coming in until the clipboard landed on the desk, making him jump. “Seriously, Cas. Are you okay? You look like you’re ready to have an anxiety attack or something.”

Cas watched the man and gulped nervously. “No...not particularly.”

“Anything I can do to help?” Dean offered.

Cas scoffed. “Not unless you wanna take a blow job as payment for all the trouble.”

“That could be arranged.”

Cas blinked and looked up at him, red faced and shocked. “I uh--” He just gulped thickly as Dean smirked to him. “I didn’t--”

“Cas, I’m already rock hard thinking about you sucking my dick. You don’t have to, but you did put the offer on the table,” Dean teased. Cas didn’t move at first, simply too surprised as Dean sat on the desk, opening up those bow legs for him to slide between. The man just quirked an eyebrow at Cas and the poor guy could only think to himself how this was the best fucking day ever.

He stood and kissed Dean, making the man hum softly in pleasure. Dean’s hands landed on Cas’ hips. He shivered as he tasted Dean’s lips, noting the hint of some peppermint gum. He vaguely thought in the back of his head whether or not Dean actually hoped he would do something like this.

Dean groaned and grabbed at Cas’ ass through the suit trousers and pressed his hips against him. Cas whined and nipped at Dean’s lip before moving to his knees.

“Shit, Cas,” Dean whispered as Cas mouthed along the jeans. “No idea how hot you look in that suit. Want you to fuck me in it.”

Cas quirked an eyebrow up at him. “Oh? So you like the idea of being bent over and fucked by a customer of yours?” Dean whined. Whined. Cas shivered and pushed up Dean’s shirt, licking at the soft stomach exposed to him. “Pull out your cock for me, Dean.”

Dean let out a breath and stood up, unbuckling his jeans and shifting his cock out. Cas licked his lips at the sight and smirked up at him. Dean gulped as he watched the man’s tongue tease the slit of his cock. “Fuck, Cas,” He whispered.

Cas then licked along the shaft, learning his taste before sucking his cock into his mouth. “Fuck, Cas!” Dean moaned, reaching down and tugging at his hair.

Cas bobbed his head along the dick, sucking and hollowing his cheeks. His hands rubbed against the denim clad thighs as he blinked his blue eyes up at the mechanic’s freckled face. Dean moaned softly and watched Cas suck hard on his cock.

“God, that feels so fucking good,” Dean moaned softly. Cas swallowed and slid Dean’s cock further into his throat, making the man moan. “Oh holy shit. Fuck, gonna make me blow, Cas.”

Cas growled around him before bobbing his head faster, ignoring the small ache in his jaw. His hands slid from Dean’s thighs to his ass, squeezing and rubbing methodically. His fingers teased between the cheeks before sliding one hand into Dean’s underwear. He rubbed at Dean’s tight hole and Dean grunted, his cock pulsing and his orgasm suddenly hitting. Cas moaned as he swallowed his load and nearly choking. He pulled back and licking his lips as he panted.

Dean slumped against the desk, cheeks red and still shaking a slight before smirking. “Shit, Cas.” He chuckled softly. “Guess I should fix your car soon.” Cas smiled sardonically. “Oh you’re definitely not getting away with a number though. I still want you to bend me over.”

Cas smiled and got up, kissing him, pressing his hips against him, making the mechanic whine again. “How about after your shift? I’ve had a bad day and you’re making it better.”


	4. Square Filled: SingleParent!AU

**Summary for the Chapter:**

> Y/N has been babysitting Mr. Winchester's son, Benny, while going to school. She can't help her crush on him, and certainly won't deny it after she tucks Benny to bed and he comes home, giving her THAT look...
> 
> Triggers: Smut. Daddy!Kink. Age difference. Dad!Dead x CollegeStudent!Reader

“Dad lets me have three oreos after dinner!” The kid boldly announced.

You raised your eyebrow to him, not entirely believing him. “Oh? He does?” You asked instead.

It wasn’t unlike this kid, Benjamin Winchester, to tell small fibs to get away with little things. His dad, Dean Winchester, thinks he’s rebelling after the divorce. Apparently a bad fight with the mom led to it.

“So, if I call your daddy, he can tell me that it’s really three?” You asked, raising an eyebrow to him. Ben seemed to pale at that, making you smirk. “Or were you fibbing?”

Ben blushed and hurried out of the room. You could only chuckle as you did the dishes. You were lucky your history teacher, Mr. Novak, recommended you for the babysitting job. What he failed to inform you of was how handsome Mr. Winchester was.

You blushed a little, thinking about how you’d wished he’d kiss you. After that, you were pretty sure you’d ride him through every orgasm.

You just hoped you could get through the night. You were wearing a skirt this time around, a lacy thong hidden beneath as a shirt hugged your curves. It was a dare from one of your friends. Which worked out. Dean was going out with Castiel for drinks. You definitely noticed the gulp when he saw you as he opened the door.

Soon though, Benny was in bed. It was nearing 11 pm. You caved and let him stay up just a little bit longer to keep you company. You sat in the living room, listening to the news as you worked on some of your homework.

It was nearly midnight when the rumble of the old Impala reached your ear. The headlights glowed and you started packing up your things. Dean was coming in as you were slipping your textbook into your bag.

He smiled to you, making you blush a bit. You composed yourself and smiled. “Hi, Mr. Winchester,” You greeted. “Benny is already in bed.”

He hummed and cleared his throat, his own cheeks red. He was probably drinking. “Good. He wasn’t any trouble?”

“Well, he did try to con me into giving him three oreos after dinner. But he successfully conned me into letting him stay up til about 11,” You admitted, shrugging. “I told him he’d have to deal with it in the morning.”

Dean chuckled, nodding. “Yeah, he’s got soccer.” His eyes scanned your body. “You ever play sports?”

“Swim Team. It’s actually how I’ve got an athletic scholarship,” You told him, your chest swelling in pride.

Dean let out a soft laugh, approaching you slowly. “Damn. Smart, strong, and beautiful,” He muttered. “How the hell is it you’re still single?”

“Most guys my age think I’m too busy. I don’t see how I am,” You said with a shrug. He hummed and you could smell the alcohol on his breath. You knew you were supposed to stop him when he started leaning in, but the taste of whiskey on his tongue pulled you in.

Dean’s hands gripped your waist as he pulled you against him. “Fuck, Y/N,” He whispered, kissing your jaw. “No idea how sexy you look in this little skirt.” You whimpered as his stubble brushed against your cheek. “Tell me to stop and I will.”

“Please don’t,” You begged, pulling him back for a kiss.

Dean groaned and held you against him before he smirked. “Ever done body shots?” He asked wickedly. Upon the innocent shake of your head, he lifted you up, wrapping your legs around his waist as he walked to the kitchen.

He set you down on the counter and pulled out some Fireball from the cabinet. “Usually, people use tequila. But I hate that shit.” You shivered, not realizing how much hearing him cuss would turn you on. “Makes me pretty violent. You don’t want that do you?”

“No, Sir.”

Dean seemed to frown at that before leaning close, cupping your chin in his hand. “Let’s try something else, Sweetheart. C’mon, Y/N. What do you really wanna call me?”

You blushed brightly, heart thudding hard against your chest bones until you mumbled. Upon a coaxing squeeze to your throat, you finally moaned out, “I wanna call you ‘Daddy,’ please.”

Dean groaned and kissed you again before unscrewing the whiskey bottle. “You’re so fucking hot, Babygirl. Take off your shirt for Daddy?” He asked, tugging at your shirt. You quickly did so, watching his eyes light up with excitement as his tongue dragged across his lips. “Damn, Y/N.”

You bit your lip, giving your chest a slight wiggle. “Do you like it, Daddy?” You asked, letting him see the way your bra made your breasts swell.

“Hell yeah I do.” Dean carefully poured the whiskey over your chest, making you gasp from the chill. He smiled and set down the bottle, eying the amber liquid that shined on your breasts and the trail that went down and into your belly button. “God I wanna taste you.”

“By all means,” You said, giving your own nervous smile.

“Won’t do anything you don’t want, Babygirl,” He assured you before dropping to his knees. His tongue dipped into your belly button, lapping up the alcohol. He smirked at the sharp gasp of surprise before he began to slowly lick up your body.

You whimpered and moaned softly, letting your head fall back as your fingers pushed into his blond hair. “Oh god,” You whined as his tongue trailed up to your neck before taking your earlobe into his mouth.

“You taste real good, Babygirl. Wanna taste me now?”

“Please, Daddy?” You begged, pouting a slight.

Dean growled and stepped back, quickly stripping until he stood before you in his pants. You blushed as you studied his toned body, biting your lip. You carefully poured the whiskey at the dip between his collarbones, watching the liquid streak down his body. You just smirked and bent down, starting at his hips and licking up, catching it before it even passed his ribs.

“Fuck, Y/N,” He moaned. He watched you lick up his body, your eyes looking up at him almost innocently. “God, I’m gonna corrupt you,” He huffed out as you finally licked at his collar bone.

“Please, Daddy?” You asked playfully.

Dean smiled and kissed you again, pulling you tight against him. “Hold onto me, Babygirl.” You did so and he lifted you from the counter with one arm, his free hand grabbing the whiskey as he carried you to his bedroom.

You were feeling buzzed after the third shot off his skin. You were practically rutting against his thigh. “Dean, please,” You begged as you kissed up his neck. “I need it.”

Dean smirked and moved so he was between your legs, kissing your thighs until he saw the lacy thong. “Shit, Baby. Were you hoping for me to fuck you tonight?”

You keened as he nipped at your inner thigh. “Fuck...Yes, Daddy. Been wanting you so badly.”

Dean growled and pushed aside your thong, licking at your folds eagerly. You moaned softly at that, his lips wrapping around your clit gently. The suck made you nearly cry out, only covering your mouth to muffle the noise as you remembered this man’s son was sound asleep down the hall.

“Dean...ah…” You moaned quietly. His tongue moved down and pushed into your wet hole until you were gasping. “Please, Daddy. I need you.”

Dean sat back and unbuttoned his pants just enough to push the denim and fabric of his boxers aside. You groaned at the sight of his length. Not only was his long, he was thick. “Fuck, Dean,” You whispered, licking your lips.

“Wanna taste it, Babygirl? Or do you wanna wait until after it’s dripping with your cum?”

You shivered and let out a breath. “After. I need you to fuck me, Daddy. Right now.”

Dean kissed you again and moved carefully between your legs, your skirt falling around your hips as you wrapped your legs around him, rubbing himself against your heat. “Fuck, you’re so fucking wet.” He carefully pushed into you, leaving you both gasping as the sensation quickly sobered you up. He moaned as his hand gripped your hip. “So tight…”

You were whimpering and moaning breathlessly. His cock was stretching you in the best way and you couldn’t help but clench around him, feeling all of him. His lips were placing gentle kisses against your neck.

He gave a quick thrust, making you gasp loudly. His smirk made you whine loudly and he was fucking into you quickly, as if challenging you to cry out for him. “So fucking sexy...God I wanted to pounce you when you walked in,” He moaned. He gripped the skirt, giving him the hold he needed to pump into you quickly. You quickly covered your mouth with your hands, back arching off the bed. “Just wanted to bend you over the couch and fuck into you all night. Couldn’t… Oh...Couldn’t stop thinking about you while I was at the bar...Fuck.” He pulled your hips up into his lap, the angle pushing him right against your g-spot. He watched you shake as your eyes rolled back in pleasure. Dean smirked and rubbed at your clit as he moved. “Gonna fuck you out, Y/N. Gonna fuck out that pretty little body of yours. You like that?” When you only whined, he gripped your wrists and pinned them over your head. “I asked a question, Babygirl.”

“Fuck yes, Daddy. Fuck me out! Please I’d love it so much!” You rasped out, clenching up around him as he rubbed your clit.

Dean smirked as he growled, thrusting faster into you. “Shit, Baby. You’re so fucking tight. Daddy needs to cum soon. Fucking cum, Y/N.”

“Oh, Daddy!” You gasped and he kissed you, muffling your moan as he thrust harder into you, riding out your orgasm. His hips began to stutter and you nipped his lip. “Daddy, I wanna taste you.”

“What?” He moaned, rolling his hips faster.

“Cum in my mouth please.” You begged, rocking against him.

Dean groaned and pulled out, moving quickly until his cock head was against your lips. You stuck out your tongue and felt the first load shoot out into your mouth, catching on your lip. He stroked himself, working out every drop for you to taste before pushing himself into your mouth. You sucked and moaned, swallowing his cum then sucking his cock as it pulsed.

“Holy...oh,” Dean moaned, gripping your hair. “Fuck yes. Just like that...Ah, shit!” He grunted as he orgasmed again, his hips jerking and fucking his cum into your throat.

You moaned and swallowed around him before he pulled away. Both of you collapsed onto the bed, panting and smiling. He pulled you to him. “I should get you to babysit more,” He chuckled breathlessly.

“Only if I get this every night,” You shot back, legs a bit shaky. Dean smirked and rolled towards you, rubbing his fingers against your folds, teasing your clit. Your hips shot up in response. “Daddy,” You moaned softly.

“I think I owe you for making me cum so much in that pretty mouth of yours.”


	5. Square Filled: Stripper!Dean

**Summary for the Chapter:**

> Y/N had no idea her boyfriend had lost his job at the auto parts store, due to budget cuts. She had no idea that he’d gotten his money from tearing off his clothing and wearing some ridiculous thong for everyone, especially her friends, to drool over him. Now she knows. And Dean knows she’s pissed.

You pouted a little at the message on your screen. An apology from Dean. Bobby was keeping him late tonight again. You sighed and sent a response.

You: Ugh, again!? Dean you promised :(

Dean: I know, Baby. But you know how much I love you and I gotta help with my end of the bills at least.

You: I’m still gonna pout.

Dean: I’ll make it up to you later tonight ;)

You: Dork.

You smiled at the message, seeing that he was typing. A notification came up. It was a text from your friend in your Asian Culture class.

Belle: Look I know you said it was date night but it’s Wednesday. Ladies Night at The Pit? Jo and Ela are going too!

You pursed your lips as you read the message. You checked the message from Dean.

Dean: You know you love me though!

You: Quick question though. Nothing bad!

Dean: Do I need to spank you for it?

You: Not sure yet. But the girls are going out for drinks. Are you okay if I go?

Dean: Of course! Baby, you never have to ask permission. You know that :)

You: Yes, but it IS polite! :P

Dean: Just be careful out there.

Dean: Wait, is it Belle that organized this?

You: Yessss?

Dean: Okay. Have fun! I know she’ll keep all of you in line.

You: Hey! I’m an adult!

You: Besides. I can handle YOU.

Dean: And I love it ;)

You rolled your eyes and got up, texting Belle as you got ready. Soon, you were in The Pit. It was a pretty decent night. The beer was a bit bitter for you, so you switched to ale, much to Belle’s displeasure, but Jo’s approval.

“Dude, how are you and Sam?” You asked Ela.

She blushed and smiled. “Well...let’s just say there’s a reason I’m ordering virgin tonight.”

At that, the three of you let out cries of excitement. Congratulations were going around. Of course, Jo, being Jo, decided then and there Ela was the designated driver. He smiled and took did a cheer with all of you, downing his drink. You smiled proudly at him. It’d been three months since he’d come out, telling you his masculine name and that he had a boyfriend. Belle even dubbed him Literal Angel because no way does anyone with a name like “Castiel” exist unless he’s an angel.

Belle was of course still single, but that certainly never stopped her from ogling the male populace, though she said, and you quote “Jo didn’t count.”

That was a cat fight in itself, to be honest.

Soon though, you were getting tipsy. It was then Belle suggested that a strip club was due, since Ela was a “momma bear” now, according to Jo.

You just rolled your eyes, letting Ela begrudgingly drive the three drunk people to the strip club.

“Shit, son,” Jo muttered, smirking at one of the guys on the stage dancing.

Of course, it was a male strip club. The Stallion, to be exact. The music was pounding hard around you. You had to admit, though you weren’t a personal fan of Snoop Dog, the remix wasn’t too intolerable. Belle got everyone drinks, Ela some water though, not very trusting of the virgin drinks in this bar, though you couldn’t entirely blame her.

You sipped at your margarita, eying the dancers. But one dancer stood out. His body was perfectly sculpted and he rolled his hips languidly towards one of the paying women. He was practically taunting him.

Rage suddenly seethed through you when bright lights flashed from the stage, revealing the dancer’s face. It was Dean. Your Dean. Dancing for money. You weren’t some prissy woman, but the thought of others drooling over your man suddenly had you shaking with anger.

You waited until he met your gaze, watching his sun-kissed face pale a slight. You simply gave him a look as Dean gulped thickly.

“You’re in trouble,” was all it said.

\--

You waited in the living room, sipping at the bottle of water in your hand when the keys jingled at the door. You looked up, meeting Dean’s eyes again as he came in. He had the dignity to look ashamed as he came in, locking the door and coming to you.

“Y/N, let me explain,” He said simply. You straightened your shoulders, silently imploring him too. He sighed. “I lost my job at the shop. I...I just couldn’t tell you. I mean, I know how bad it is. You’re stressed out as is with school and work. The least I could do is try to find another job. I know the owner and he promised me at least five nights a week.”

You took a deep breath, watching him gulp thickly. “Dean, I can handle that you strip for cash. Hell, I can swallow my pride and let girls drool over you more than I get to even see the man I love. What I cannot handle, nor will I tolerate it, is when my boyfriend lies to me five nights a week about where he is.” You stood, approaching the man. You were by no means tall, but the way the man shrank under your gaze made you feel like a giant. “Dean, what if something happened while you were there? What if the place caught on fire and you died in there?”

“Bit drastic,” He muttered, giving you a sheepish smile. You glare hardened, making him shiver. “I know, Baby… I should’ve told you when it happened. I just didn’t want to disappoint you.”

You let out a breath, grabbing a bottle of water and giving it to him. “You’re probably thirsty after all that flaunting you’ve done.”

“Y/N--” He tried reaching for you.

“Down,” You said, your voice leveling. His shudder made you smirk. “Maybe I should show you just what happened when little boys lie to me.” He bowed his head to you, gulping. “Safe word?”

“Impala,” He rasped out. You smirked upon seeing the way his cock hardened under his jeans. Your hand cupped him, rubbing him through the jeans. “Fuck, Y/N--Oh!” He grunted when you squeezed firmly.

“You enjoy dancing, don’t you?” You asked, trailing your free hand along his hip as you kept rubbing and squeezing him. “Like rolling your hips for every girl to see?”

“No, Ma’am.” He whined as your nails scratched his skin.

“Then why do it? Why push your cock into their faces? Don’t you know it belongs to me? Well?”

Dean groaned when you squeezed again. “I’m sorry, Ma’am.”

You pulled back. “Go take a shower. You smell like that brothel.” You snarled out, heading for the bedroom.

Dean let out a breath he hadn’t realized he was holding. He knew he was in trouble...but, God, did he love it when you were mad at him!

He hurried into the bathroom, stripping down and scrubbing his body in a way too hot shower. He hated working at the club. Too many women he didn’t know wanting to touch him. Too many germs on the poles themselves. He felt like he needed to bathe in rubbing alcohol.

The fire in your eyes as you looked at him from the bar made him shiver in a way that some of the women thought he liked it.

As tempted as he was to jerk off then and there, he knew better. He knew you wanted him all to yourself. Instead, he rinsed off, ignoring the ache of his cock and stepped out, drying and wrapping the towel around himself. Once he was in the room, he saw you sitting on the bed, looking disinterested in his nearly naked body standing before you.

He dropped the towel and crawled up the bed to you. “Y/N,” He whispered, kissing your cheek. You looked at him, examining him. His skin was red from the scalding shower, but you could still see the freckles poking out. “I’m all clean for you.”

“Good. Lay down.” You ordered. He did as you asked, laying on his back. He watched you strip down until you crawled up his frame. He licked your inner thigh lovingly as you straddled his head. “Make me cum.”

“Yes, Ma’am,” He whined before getting to work on your pussy.

He reached up, gripping your hips as you rocked them down. He moaned softly, hips twitching in a desperate need for touch. You smirked as you moaned softly, rocking against his lips. His fingers trailed along your back, rubbing at the muscles that began to twitch in response to the stimulation.

Dean thrust his tongue into you, shaking his head. You gasped, his stubble scratching against your folds and his upper lip rubbing against your clit.

“Fuck...that’s it, Dean...God, I’m gonna cum,” You moaned, thighs giving a slight tremble as he moaned into your cunt. You whined and tugged at his hair as you shook and orgasmed.

Dean moaned and gripped your ass as he tasted your juices on his tongue. He moaned as he felt some escape and fall onto his tongue. You were whining and keening over him. He groaned and moved you, kissing you as you straddled his waist. Your cunt, slick and still throbbing, rubbed against him.

“I love you, Dean,” You whispered against his lips. He opened his mouth to speak but you sank onto him, moaning with you as his back arched. Your nails dug into his chest as you panted, biting your lip before you began to ride him.

“Fuck, Baby! Oh!” He moaned loudly, not entirely prepared for you to suddenly move so quickly.

You felt prideful, knowing you got him like this. “You’re mine,” You groaned. “Only I get this right?”

“Yes! Yes, Y/N! Fuck yes!” He moaned, shaking and gripping your thighs.

For a long moment, nothing more was said. Just the rasped out “Yes!” between the two of you and the whine of each other’s names.

You were rocking your hips faster before groaning as you orgasmed again. Dean was losing control of himself and moved you, pulling out and stroking himself until he released over your stomach. You panted with him and practically collapsed onto him, kissing him and whining quietly.

Dean was holding you, kissing your head and rubbing his fingertips along your back gently. “I love you so much, Y/N,” He finally whispered. “I’m sorry you didn’t tell me. I just...you’re so busy with school and work and you were stressed about bills, I--”

“Dean, hey,” You interrupted gently, looking up at him as you laid your head on his shoulder. You sighed. “As long as you don’t screw some girl for flashing a few twenties, it’s okay. I just…” You blushed. “I might be a little possessive over you. And, I mean, seeing my friends drooling over you was…”

Dean smiled, lifting your chin and kissing the tip of your nose. “You’re so cute when you’re jealous.”

You huffed and nipped at his jaw, making him groan. “You’re still in trouble, Winchester.”


	6. Square Filled: Prince!Sam

**Summary for the Chapter:**

> It is the final battle between Heaven and Hell, and the brothers stand on opposing sides.
> 
> Triggers for DEATH and BLOOD.

It was so long ago now that the gods laughed at them.

Brothers. One of Heaven. One of Hell.

Dean could only stare as he saw the flames of the armies of Hell coming towards his forces.

Heaven VS Hell.

How could Fate be so cruel?

Soon, he would be staring down his own brother. The one he’d protected for so many years, since the general, Azazeal, killed their mother.

This was a joke. This was a cruel fucking joke.

But there he was, veins black as demon souls and a sword in his hand.

His baby brother.

Dean swallowed his pride. He had to. This was way more than what he’d ever had nightmares of. This was the reality. The reality was that if his brother won, the world would end.

The demons would take their claim on the Earth, and everyone would die.

This was the final stand between Heaven and Hell.

Sam let out a roar that sent chills through Dean’s soul. He gave a final prayer of hope before meeting the once innocent boy he’d raised blow for blow.

Their swords sang and sparked as they slid and beat against one another. Sam had kicked Dean’s gut, making him stumble back. The eldest just barely dodged the strike. His lip twitched up into a snarl as he felt a bit of skin slice.

He was already tired of fighting demons. But now, the battle seemed to move away from them as they clashed.

His chest burned with the blessing he’d received from the angel who’d healed him in the last battle. His dear friend. He wondered briefly if he could find him somewhere on this battlefield. His mind wandered off, wondering if he would find him alive.

Sam smirked, seeing Dean’s mind straying, and took his chance. The look of shock on the man’s face was somewhat satisfying, become more so when the blood gurgled from his lips.

Dean grunted as his heart tried to beat around the blade, losing his sight. He could vaguely hear a shout of agony in the distance.

Castiel… He realized.

Sam watched as Dean’s hands reached up, gripping his shirt. “I’m...sorry,” Dean rasped out.

The Prince of Hell scoffed and ripped the sword from his chest, shoving the body down into the blood-soaked dirt. The battle around them froze in shock as Sam stood tall, his sword dripping with the blood of his brother.

A wicked smile drew across his face. “Take no prisoners,” He ordered simply.

The demons all cried out joyously and begin to slaughter Heaven’s armies. What angels remained had fled. He did manage to catch sight of a rather broken looking angel with blackened wings, flying with the help of his brother.

Sam watched them rely on one another and could only scoff in disgust as he stepped over the corpse of his own.

Heaven has fallen...Hell will rise.

Aesthetic I had created for this:  
https://78.media.tumblr.com/c21649820eda777250854f687728676a/tumblr_p4j4wlr96a1v3puivo1_1280.jpg


	7. Square Filled: Zookeeper!Cas

**Summary for the Chapter:**

> Cas is the caretaker of a pregnant tigress at the zoo and his girlfriend and her niece are visiting.

“Auntie Y/N! Auntie Y/N!” Vivian squealed excitedly as she saw the prowling lions walking around their habitat. “Kitties!”

You couldn’t help the smile that drew across your face as you nodded. “Yes. Those are pretty big kitties,” You cooed to the three-year-old.

Vivian clutched at the chain link fence, separating her from the lions as she pressed her face to it to get closer to them.

A deep chuckle behind you startled you at first but you smiled as you saw that it was only one of the staff. “Castiel, you startled me,” You chuckled.

This grabbed Vi’s attention and she whipped around so fast, her little dress billowed like an opening flower. “Uncle Cas!” She yelled, charging at him.

Cas laughed and scooped up the toddler, setting her on his hip. “You got your auntie to take you to the zoo?” He asked as he approached. Vivian nodded excitedly.

You smiled fondly to your boyfriend. You’d only been together a couple months, but Vivian has already taken to calling him “Uncle Cas” since he was with you. Of course, there was definitely no downside to it. She was latched onto him and the ease in which he took her into his fold was heartwarming.

You approached and kissed his cheek, making him smile fondly to you. “I figured it’d be a good surprise. She wanted to see the cats,” You chuckled.

Cas smiled. “I knew you were plotting. You already trying to see if I’m flirting with other girls?” He teased.

“Oh. I know you are,” You said, giving him a smirk. “How’s Shoana doing?”

Cas gaped at you but you could see the mirth in his eyes. “What Shoana and I have is completely different!” He laughed.

“What’s a Shawn-Ya?” Vivian asked cutely.

Cas smiled. “Shoana,” He corrected gently, working her through the pronunciation. “And it’s pretty tiger girl. She’s getting ready to be a mommy.”

“KITTIES!” Vivian squealed, squirming. “I wanna see Shawn-Ya! Shawn-Ya!”

You smirked. “You better show her before she loses her mind,” You laughed. Cas smiled and set her down, leading you both to the habitat. Sure enough, there was a tiger lazily laying out in the sun. Vivian cooed happily as she pressed her face to the fence again. Shoana’s ear twitched in Vivian’s direction, tail swishing slowly. “Is that normal?” You asked.

Cas smiled. “Yes. She’s been really tired lately. But she’s nearing the end of it. Unfortunately, I’m the only one she lets get near her for feeding,” He said with a shrug.

You smiled and wrapped your arms around him. “Well, it’s good to know that if we ever have such a thing growing inside me, you’ll take good care of me, right?”

“I think I’d rather face the tiger,” He teased, making you huff softly before he kissed your forehead gently. “Besides, I think keeping you in a cage might make you maul me first.”

“I mean, probably,” You snickered. “You’re off soon right?”

“Yes?”

“Why don’t you show me the same love you show your favorite tigress once I take Vi home?” You asked, smirking as his eyes darkened with desire.

Cas smirked, muttering lowly, “Sounds like a date.”


	8. Square Filled: Lifeguard!Cas

**Summary for the Chapter:**

> When an Alpha comes across an Omega in heat walking in his area, he decides to help him out, as he had sworn to do.
> 
> ABO-VERSE. SHAMELESS SMUT.

The beach was always fairly quiet. That’s actually why he picked this spot, in particular, to be on post. People seldom came through this area. This meant, fewer people were likely to drown on his watch. And that meant Cas could just go out into the water and surf as much as he liked.

It was on a particular day that a scent suddenly hit him and he saw someone walking on his beach from the watchtower. The man looked anxious as he walked around, his head darting this way and that.

Cas frowned and pushed himself to move. It wasn’t until he was standing a good five feet from him that he realized the smell was this man’s Omega scent and his flushed face wasn’t the result of the sun, but his heat.

“You shouldn’t be outside,” Cas said, his voice coming in a low rumble.

The man shivered as he looked up at him, green eyes clouded with want. “I know...I...I didn’t know it was coming.”

Cas’ nose twitched a bit as he forced himself still. Above all else, he was someone who swore to help others in need. But what could he do?

He had an idea, but nevertheless, he asked the Omega.

\--

“Fuck yes!” The Omega, now known as Dean, cried out.

Cas grunted as he fucked him. Dean was bent over his desk in the watchtower, taking every inch of his cock eagerly. The Alpha carefully dragged his nails up Dean’s back, watching the man mewl happily.

“Such a sweet Omega,” He moaned, pushing deeper now. Dean gasped and clutched at the edge of the desk. “God, you’re so tight.”

“Yes, Alpha. All for you!” Dean moaned, spreading his legs wider for him to take everything Cas had to offer. “Please...Oh fuck, please!”

Cas smirked. Something about the way this particular Omega was begging for him was just so very satisfying. Cas groaned and grabbed his ass, spreading the cheeks wide to watch the rim stretching around his thick dick.

“So fucking hot,” Cas moaned, seeing the slick escaping and soaking him. “Look at you, Omega. You’re so desperate for a knot, you’re making a mess.”

Dean whined, shaking at that. “Alpha, don’t tease me!” He whimpered, rocking his hips.

Cas smirked, watching the way Dean was fucking himself onto him. “Oh, I’m not teasing. Not yet. I wanna see how pretty you look cumming on my big alpha cock.” Dean was red at that when Cas pulled back, only the tip of his length buried into him. “Show me how bad you want it.”

Dean groaned and started to thrust his hips back against him, taking in every inch he could as he clutched to the desk. Dean was so relieved to have found this Alpha today. In truth, he’d been terrified of some other Alphas scenting him and dragging him off to use him. But finding this lifeguard might’ve just saved his life. He loved how he restrained himself and made sure he absolutely wanted it before pulling Dean against his body and kissing him.

Now he was standing in the tower, riding hard against some random alpha’s cock as he panted and whined, desperate to be filled.

Today was a good fucking day.


	9. Square Filled: Hospital!AU

**Summary for the Chapter:**

> Cas loses his first patient.
> 
> Triggers for blood, death of a minor.

“Start the defibrillator!” Dean ordered.

Cas nodded and hurried to the machine, charging it up as Dean tried to use chest compressions to revive the patient as another nurse used the oxygen mask to try and push air into the teen’s lungs.

A car wreck. It was a damned car wreck. Some drunk driver hit this seventeen-year-old and now he was dying.

Cas moved quickly, focusing on his job. He needed to focus. He needed to calm down and focus on the task at hand.

The machine beeped as it fully charged to seven-hundred volts. “Charged,” Cas said, grabbing the paddles.

“Clear!” Dean ordered before Cas pressed the paddles to the boy’s chest. The kid convulsed a slight, back arching off the table before slumping again. Dean’s eyes darted up to the electrocardiogram. A straight line glared at him in protest. “Up it to one-thousand,” He ordered Cas, returning to trying to use the chest compressions.

Cas let out a breath as he got the machine to start the charge again. The long, nagging tone was echoing in his ears as the blood rushed through him. Adrenaline. His adrenaline was pumping to a point of making him nauseous.

“Charged!” He announced, his voice wavering as he approached.

The doctor ordered, “Clear!” just before Cas pressed the paddles to the kid’s chest.

Again, the body convulsed, but landed hard and limp against the table. Cas was about to up the voltage when he heard the doctor’s soft voice say, “Call it.”

Too late. Too much time had passed.

Cas gulped thickly as the woman documented the boy’s time of death. Death. No, that wasn’t right.

“Are...Maybe if I--”

“Cas,” The doctor said softly. Cas shuddered and looked up at Dean’s sorrowful eyes, the ones that said simply “there’s nothing more we can do.”

Cas solemnly nodded and rested the paddles in the holders before shutting down the machines. Nothing could be done.

He knew that. There was really no way the kid could’ve survived.

But he had found himself in an empty supply closet, clutching at his own arms for something of a comfort as tears streamed down his face.

The door opened and he froze, meeting Dean’s gaze. “I thought so,” Dean sighed before coming in and closing the door. He pulled Cas into a hug.

“I...I’m sorry,” Cas sniffled.

“A mother,” Dean said. Cas blinked in confusion. “That was the first one I lost. Her daughter was beautiful...but we couldn’t do anything to save the mother. I cried for days.”

Cas let out a soft whimper. “The first is always the hardest right?” Cas asked, his voice breaking a bit.

“They definitely don’t get easier.” Dean pulled back, smiling gently. “How about you and I go for a drink after our shift?”

Cas let out a watery laugh. “You’re asking me on a date after that?”

“You’re emotional. Seems like a good time to con you into bed,” Dean teased, making Cas flush. Dean gave a smile and squeezed him again. “Let’s get you cleaned up.”

 

Aesthetic: https://78.media.tumblr.com/72e7d9043a6a554d74735f359b5bfa17/tumblr_p4j75pI6Xc1v3puivo1_1280.jpg


	10. Square Filled: Music Teacher!Dean

**Summary for the Chapter:**

> Dean's got a student that doesn't really open up. What he learns about this kid pushes him into doing something big.
> 
> Triggers for attempted suicide and signs of abuse.

Fingers plucked at the cords, Dean’s eyes focusing on the positioning of the kid’s hands. He was doing pretty good, actually. He smiled, nodding in approval as the boy finished the riff.

“Great job, Y/N. Let’s try going to dropped-D now.”

Y/N nodded, reaching up to tune the ¾ guitar. Dean watched the kid, studying him a bit. He wasn’t physically unhealthy, but Dean could just tell that there was something wrong with him. Not in an “FBI Most Wanted” way but more of a “Why does he look so sad?” way.

Dean watched as Y/N tested the open cord before he began to play. Y/N didn’t really talk. Like, at all! In the months that Dean had been teaching him, he was always silent, but Dean could see the love for the small guitar in his hand, briefly wondering if it had been gifted to him by someone.

In the end, when Dean had tried talking to him, he got no response, just a blink of confusion. Dean sighed and finally got on this system when he’d ask something; make sure it was a “Yes or No” answer question.

Dean smiled to Y/N as he finished. “I got some soda for us.” Y/N perked up at that. Dean liked to imagine that, if he had a son, he’d be like Y/N, in that, he was excited in his own way. Dean passed the soda to him, watching the kid bow his head in gratitude and before opening the soda and nearly chugging it.

Dean chuckled, drinking his own. It was when Y/N was chugging the last few drops that his sleeve slipped down. Dean’s eyes widened and he grabbed the kid’s arm gently. “Y/N...pull up your sleeve.”

Poor boy. He froze like that, paling almost in horror. He shook his head quickly, making Dean frown. Dean sighed, releasing his arm. Y/N seemed to relax, but Dean started asking questions.

“Y/N, you know cutting yourself isn’t okay, right?” He asked simply. Y/N’s eyes fell a bit, dimming with guilt as he nodded. “I know you don’t like to talk but...the reason for that...is it the same reason you hurt yourself?”

Y/N nodded slowly, starting to bite on his cheek. “Y/N...are you safe at home?”

Y/N didn’t move, nor did he meet his teacher’s eyes. He just stared at the guitar in his lap, clutching the empty soda can in his hands. 

Time was up for the day, Dean knew. He couldn’t keep him there much longer. Y/N was always very particular about time, always glancing at the clock. Dean remembered a day when they were running behind and Y/N looked so anxious…

Dean reluctantly lets him go, telling him to practice the riff they were working on for the next week.

However, that week had passed and Y/N was nowhere to be seen. Dean tried to push aside that worry.

But that one missed class became two.

Then three…

Now it’d been a month since Y/N had shown up for the class. Dean checked the time on that fourth class.

Nothing.

Dean sighed and tried to contact his family, but no go. Instead, he tried to call the school. Legally, they couldn’t give him anything.

Dean had all but given up until this kid showed up. “Hey,” She barked, looking more pissed off than anyone he’d ever met! “You Y/N’s guitar teacher?”

Dean blinked at that. “I am. Who are you?”

“Claire Novak. I need you to give me a ride.”

Dean frowned. “Nice try, kid, but--”

“You wanna know where Y/N is and I’m not allowed to go without an adult. So c’mon! Two birds and all that crap, right?”

And that was how Dean found himself in a car with some random teenager driving down at least two hours away. He dearly hoped he wasn’t about to get arrested for kidnapping.

However, he blinked as they arrived at a psychiatric treatment center. Dean looked at Claire. Her face was blank as she stared at the doors. With a deep breath, she got out. “Let’s go,” She said, slamming the door shut.

Dean sighed, following her in. She did the talking, being honest. Apparently, they were on the list.

The doctor led them into a visiting area and soon, Y/N came out. He was wearing a patient’s outfit though, a bracelet fitted to his wrist. Dean gulped as he saw healing bruises all over the boy’s arms. More importantly, he saw fresher cuts, though they were faded red lines now.

“Hey, Y/N,” Claire greeted, approaching the boy. She hugged him gently. Y/N sighed and hugged back slowly. “You okay?”

Y/N let out a sarcastic chuckle at that. “Great. Finally get to eat,” He said softly.

Dean blinked in surprise. He could only stand by idly as Claire got him to talk softly about his time here. For once, Y/N doesn't look like he was dreading something. Instead, he looked happy to be alive.

Finally, Claire stood aside, letting Y/N look up at Dean. He gave a small smile. “So, I can still get lessons, right?” He asked softly.

Dean smiled. “Course, kid. But you gotta start showing up, ya know?” He teased.

Y/N’s smile widened and he rubbed the back of his neck. “My bad. Lost track of time, I guess,” He joked. Finally, he sighed and looked at Claire. “Thanks for bringing him.”

Claire nodded and soon Dean learned that Claire had lied about being his girlfriend, figuring out she was gay pretty quick. Y/N finally opened up and told Dean everything.


	11. Square Filled: Entrepreneur!Dean

**Summary for the Chapter:**

> Castiel works for Dean Winchester, a great man in his eye. But when Dean tries to play it off, Cas catches on too quick and Dean might be in over his head!
> 
> Might become a series in future. Not sure yet.

“You’re drooling,” A sultry voice cooed in his ear. Cas blinked and stared at his hands instead, his cheeks fighting against his will to not blush. Meg simply smirked in his direction. “So cute when you’re flustered.”

“Shuddup,” He huffed, straightening his shoulders. The object in which he was allegedly drooling over was his damned boss. The man simply had this swagger about him. His charisma was both a part of his charm as well as the reason he was even successful in the first place. And damn him for having that charm plus that gorgeous fucking face.

Dean Winchester was like a living, breathing Greek statue. Cas was just lucky the guy would suffer his presence for longer than five minutes! He was about ninety-percent sure the man hated him.

Usually, Dean would drop a file into Castiel’s lap then mutter something that Cas could only barely catch, typically about documentation and appointments or meetings.

The lack of words exchanged made it abhorrently obvious; Dean Winchester hates his secretary.

Cas was working on some emails when he heard Dean’s voice in his office. “Sam, I get it, but you can’t just blow up like that! You know how he gets,” He was saying.

Another fight with his brother then, Cas determined. It was something only he knew. Dean and his brother tended to fight a lot, especially after they lost their mother. Their father became a drunk, which Cas wondered had been his drive for ambition.

“Then move the fuck out!”

“Whoa,” Cas muttered as he heard the tell-tale sign of a phone being slammed into the receiver. He frowned when he heard silence and decided to check on him. Cas blinked as he saw his boss with his face in his hands. Of all things Cas had seen, stress was not one that had appeared on Dean’s face. He’d heard it through the doors, yes, but seeing it was different. “Sir?” He called out, rapping his knuckles gently on the door.

Dean blinked and looked up at him and nodded. “C’mon in, Cas. Please close the door...might wanna lock it too.”

Cas nodded and did so, thinking it was to keep someone from walking in. As he stepped forward, Dean sighed, leaning his face against a hand. “Guess you heard that?”

“At least your half of it,” Cas admitted. “You okay?”

Dean had a small smile that made Castiel’s heart break a little. “I’m about as far from it as it gets.”

Cas watched him for a moment before saying, “You two fight often, and you’re living together. Maybe him moving out would be best. You’re both grown men. I understand you two are close, but if this kind of stress becomes so very prevalent, then maybe separation is for the better.”

“Yeah?” Dean asked, as if unsure about this. He sighed and glanced down at his desk. “I just...I worry about him. He’s my baby brother, ya know?”

Cas smiled, nodding. “I understand. My own brother can be a pain in the ass when I do see him, but I do love him dearly and we protect each other.”

Dean glanced up and nodded, calming down a bit. Cas felt a bit at ease, knowing he’d helped him out a bit. “Thank you...Seriously, Cas.” He then smirked to the secretary. “Maybe I should be rewarding you.”

Cas raised an eyebrow. “Oh?”

Dean rose up and walked around the desk. Cas tensed up a bit, watching him curiously. Dean’s hips swaggered a bit until he was leaning against the desk as if trying to flaunt something for him.

“A little birdie told me you’ve got it bad for guys like me?” Dean tried.

Cas flushed brightly and made a mental note to do some horrendous prank to Meg later on. Instead, Cas snarled a bit. “I...Look, I get it. It’s not your thing, but there is no need to humiliate me like this.”

It was a prank. It was a fucking prank. Cas turned on his heel, ready to leave the office when Dean said, “No, Cas.” He froze at that. Was it him saying his name with a desperation that made him stop, or was it genuine curiosity? Maybe a bit of both.

“I…” Dean sighed, rubbing his face. “The...The last guy I dated…” Cas’ eyes widened at that as he tried to compose himself but...holy shit. Dean Winchester is into guys too?! The realization was enough to make Cas turn and look at him.

The man who held so much swagger day to day, flirting with anything that had tits, looked sheepish and timid as he gripped his desk. His boss was shaking, Cas could now see. Dean was scared.

“I…” Dean tried again. Finally, he sighed and turned his back. “Forget it. Forget this happened. I need to make some phone calls.”

Cas watched Dean for a moment before approaching. Cas gripped his hips and pressed his own against him. Dean hissed in a breath and shuddered as Cas’ lips grazed the shell of his ear.

“If I have you, I’m going to fuck you properly in a bed,” Cas muttered lowly into his ear. “And when I do, I’m going to treat you much better than any arrogant prick ever did. Got that?”

“Yeah...Yes, Sir,” Dean sighed in relief, pressing against him.

Cas hummed and pulled away, his chest swelling with pride as he headed for the door. “You’ll have an email with an address by tonight, Mr. Winchester. But forewarning, I’m a bit more intense than you bargained for.”

Dean listened to the door open and close, Cas leaving his office. He simply stood there, absorbing what had just happened. He thought maybe he’d give Cas a blowjob but Cas wanted to thoroughly fuck him.

Dean gulped and had to grip himself in his pants, feeling the ache of his cock straining against the slacks. This was going to a long rest of the day.


	12. Square Filled: Veterinarian!Cas

**Summary for the Chapter:**

> It’s an ordinary day for Castiel and his assistant, Charlie, when a little kid runs in crying with a small bird in her hands!

“Uh, Cas!” Charlie’s voice called from down the hall. “I think I might need your help with this--” Her voice was covered up by what sounded like a frantic child.

“But you’re wearing doctor’s clothes! Aren’t you a doctor!” The little girl’s voice wailed.

Cas hurried in, expecting to see some embarrassed parent looking sympathetic and mournful over their daughter’s desperate reaction to help their pet. Instead, a child was angrily staring down Charlie, looking for answers, with no adult in sight.

Cas took a moment, seeing the box in her hand and hummed. “I’m actually the doctor. Charlie here is my assistant,” He explained, grabbing the girl’s attention. Charlie looked relieved that the man had shown up. “What seems to be the problem?”

The girl pursed her lips, staring at him for a moment. “Are you really a aminal doctor?” She asked adorably, making Cas smile.

“I am. My name is Doctor Castiel. How can I help you?” He asked, smiling proudly at her.

Once the child deemed him suitable enough, she held up the box. “It’s hurt. Fix it.” She demanded.

Cas lifted the lid carefully, seeing a small bird wrapped up in socks with a dirty worm squirming by it. Its wing was bent at an awkward angle.

“How’d this happen?” He asked as he examined the bird.

“It fell cuz it sucks at flying.” Charlie choked on her laugh, making Cas’ lip twitch up at the corner. “It’s not funny!” She huffed, looking at Cas. “You help aminals. Fix it.”

Cas smiled. “I’ll do what I can. But, while I’m checking on the birdie, where are your parents at?” The child paled a bit, looking down at her shoes as she shifted, looking guilty. “Did you run here without telling them?”

“Maybe?” She mumbled.

“Alright. What’s your name, kiddo?” Cas asked as he carefully took the box.

“Y/N.”

Cas smiled. “A lovely name. Now then, why not give my friend there your parents' phone number and you can help me out. Sound good?”

Y/N lit up immediately and nodded, hurrying to Charlie and rattling off the phone number quickly.

Soon enough, a rather large man hurried in. However--

“Sam! Wassup!” Charlie greeted. “Guessing, Y/N’s yours?”

“Charlie Bradbury...holy crap, hey!” He said, sighing in relief. “Yeah. She is. Where is she?”

“Helping the doctor with a broken wing on a quail,” Charlie replied as she led the man in.

Sam peeked into the door, seeing his daughter’s focused expression as Cas showed her what to do, careful of any pain the bird might feel.

“There you go.” He said gently, watching the bird get comfy with its wing wrapped against its body.

“But...how can it fly like that?” Y/N asked, scowling.

“Well,” Cas began. “It can’t. Not yet anyway. It needs lots of rest and food so it can heal properly.”

“Oh...so like when Uncle Dean broke his leg but Dad said he cried like a baby the whole time and wouldn’t sit still?”

Cas blinked then snickered, nodding. “Yes. Just like that. The birdie here needs to rest and not cry like a baby though.”

“How long?”

“About a month.” Y/N gaped and pouted. “Don’t worry. How about this; when it’s time to let the birdie go, I’ll give you a call and you can help me release it. Okay?”

Y/N smiled big. “Really?”

“You gotta ask your parents though,” He said.

Y/N nodded and Sam chose that moment to finally knock on the door. “Daddy!” Y/N squeaked and hurried to him. “Doctor Castiel said I can help him release the bird in a month! Can I? Please!” She dragged out the “please” into a high pitched whine as her eyes bugged and her lip pouted out.

Sam smiled and lifted her up. “Well...only if you promise not to run off without telling me. You scared your mom. I have to tell your uncle to stop the search you know.” He smiled at Cas. “Thanks, man.”

“It’s good to know you and Jess are back in town. When were you going to call?” Cas chastised. “And tell me about the little one? More than a Facebook post at least.”

Sam smiled. “Sorry. We just moved back a couple days ago. I’m more impressed she found the vet clinic.”

“There’s a big sign outside, Dad.” Y/N huffed, rolling her eyes. Sam squeezed her nose, making her groan. “Daddy!”

“No rolling your eyes,” He said, giving her a look. She pouted from her spot on his hip. “Thank you for watching her though,” He said to Cas.

“No problem. She’s really good with animals. If she ever wants to come over, I’m glad to watch her for a bit. Heads up though. I don’t think she likes Charlie,” He teased, pointing to his red-haired assistant who just pouted.


	13. Square Filled: GamerDeveloper!Sam

**Summary for the Chapter:**

> It’s E3 and Sam is autographing notebooks, posters, fanart, and everything in between for his greatest game series with the third installment scheduled to come out in the fall. Lo and behold, he meets one of the biggest YouTubers in the gaming industry and a huge fan of his games! He wants to show his appreciation for her.
> 
> Mature for almost one-night stand. I just couldn't write it.

You smiled as you approached the booth. Your heart hammered as the guy in front of you had his game copy signed. You gulped, clutching the notebook in your head. You were inwardly cursing yourself. You should’ve brought your game case for him to sign.

Too late now. You were up.

Sam’s eyes lit up as he saw you. “No way! You’re Y/N, right?” He asked.

Your cheeks went a bit pink as you nodded. “Nice to meet you, Sam.” You said as you opened the notebook to a blank page. He grinned. “I didn’t know you watched my stuff.”

“You’re the only one that really delves deep into all the hidden plot points of Men of Letters,” He chuckled.

Men of Letters, dubbed MOL, was a series of games that Sam Winchester had developed. The first one introduced the concept of it, getting the players tied into this huge world of monsters, demons, angels, and so much more! Each player played a Legacy, a member of MOL by inheritance. The main character of the first MOL worked as an American Legacy who came across their father’s journal and had to follow a series of journal pages that were missing through hunts of monsters tied in with the death of the father, only to find out, at the end of the game (Spoiler alert), that he was alive and had led the Legacy to him through these hunts.

In MOL 2: Apocalypse, the Legacy, and their father were tasked with hunting down demons in an attempt to stop Lucifer from rising!

With MOL 3 in the works, the hype around the series was incredible!

“Guessing you’ll be on the panel later?” He asked, glancing up at you.

“I’ll try to be. Got my own panel and the times collide a smidge.” Sam’s expression changed. You blushed and started rattling off. “I mean, I can try my best bu-but you know how panels work and everything--”

“Y/N,” He said sweetly, smiling at you. You blushed as he handed you your notebook, pen marking the spot. “Breathe. I hope I do see you later,” He said, giving you a quick wink that you almost missed as you were ushered away for the next person to meet him.

You were smiling and flustered as you walked away from the booth, excited. You opened up your notebook, excited to see his signature. While there was a signature, there was a message as well. 

#407. Swing by around 8 tonight?

You gulped, staring at it. That...was his room number. Holy shit, Sam Winchester gave you his room number and wanted you to swing by at a crazy hour! That’s when most of the partying was happening, meaning no one would be in their rooms.

When did he have the time to write that down!

You tried not to think about it most of the day, getting to your panel and finishing it within two hours. You had unfortunately missed Sam’s panel by about forty-five minutes. Yikes!

It was 7:50 as you heard everyone bustling down the halls outside. You were pacing your room, glancing at the notebook every so often.

You wanted to go. After all, Sam was way hotter than you’d expected. If this is what you thought it was…

Then again, what if he just wanted to hang out? What if he wants to be friends? But you considered everything.

In the end, at about 8:05, you found yourself knocking on his door. Two floors above your own. You heard movement inside before the door opened. His eyes darkened as he smiled at you. “You came!” He said excitedly, letting you in.

“I figured I’d let you squirm a bit,” You joked, trying to lighten the mood as you walked in. The room was a bit bigger than your own, though that wasn’t much of a surprise. On the table were two glasses and a small wine bottle. “Expecting a hot date?”

“She just arrived,” He said softly. He smiled at you. You smiled back and he stepped closer to you. You met him halfway, his lips finding yours quickly as he pulled you tight against him. Your arms wrapped around his neck and he hummed, his hands spreading on your back before one grabbed your ass, drawing a groan from your throat. “Fuck, that’s hot.”

“Sam,” You whined. “That’s not fair.”

Sam just smirked to you. “I gotta give credit to my favorite gamer,” He said, pawing at you and groping you. “You’re fucking gorgeous and sexy as hell. No idea how hard I get when I see those cute little workout selfies of yours on Instagram.”

You moaned, pushing him against the wall. He grunted and chuckled as you kissed his neck. “No fair. You can’t have all the fun,” You muttered against his skin.

“I think you like me taking control,” He said before lifting you up and carrying you to the huge bed. He dropped you into the middle, the mattress nearly swallowing you until he was on top of you again, kissing you and pinning you down. You moaned and arched against him. “See?”

You blushed. “I...I’m not used to this.”

Sam’s eyes softened and he smiled gently. “We can st--”

“Don't you dare,” You huffed, pursing your lips. Sam smirked and gave you a peck. “I’m just not used to one-night things.”

“That’s fair. Want some wine to calm down?” He offered, tracing his finger against your hip. You smiled and nodded, both of you sitting up. You watched him walk towards the table, biting your lip as you realized he was well fit. It was hard to tell under all the layers he wore at his booth.

He poured two glasses and offered you the first. You smiled as he clinked his with your and you both sipped from yours. You made a face. “Red wine?” You asked.

“Merlot. Wasn’t sure what you’d like so I got one that was popular on the menu.” 

You smiled softly, nodding. “It’s good. Should definitely choose a red next time though. Bitter.”

Sam tilted his head as he sat beside you again. “Really?”

“Really good.”

Sam smirked as he finished off his glass. “Maybe, I should invite you over to taste it with me?”

You smiled and took the last of your wine into your mouth, kissing him and passing the alcohol back and forth. Sam moaned as you both split the drink, swallowing it down as he pulled back. “You better do that if I invite you over again,” He said, smiling.

“Then you better give me a good reason to come back,” You replied, climbing into his lap. His hands found your ass again, making you smile. “Your obsession with my butt.”

“It’s nice and grabbable. Can you blame me?” He chuckled before kissing you again.

His lips were soft as he grabbed at every inch he could of you. You gripped his shirt and finally pushed your hands under it, feeling his stomach. Shit, he really was ripped! Sam had to pull his hands away so you could push off the shirt as you wanted, making him smile as you bit your lip at the sight.

“Like?”

“Starting to think you do this for all your favorite fans,” You teased, smirking back to him.

Sam blushed a bit and smiled nervously. You blinked in surprise, realizing he wasn’t one for these things either. You smiled and kissed him. “What was that about you taking control?”

“You sure?”

“Yes. I want you to be rough with me, Sam. Make me look like hell.”


End file.
